1,2-Dichloroethane → HCID 178432867, Verbindung

HRID 1875068Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1875068
C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH2:15][CH2:16][C:17]1[C:18]([F:34])=[C:19]([O:24][C:25]2[CH:26]=[C:27]([CH:30]=[C:31]([Cl:33])[CH:32]=2)[C:28]#[N:29])[C:20]([Br:23])=[CH:21][CH:22]=1.[Cl:35][C:36]1[N:37]=[C:38]([CH3:44])[NH:39][C:40]=1[C:41](O)=[O:42]>CN(C=O)C>[Br:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][NH:15][C:41]([C:40]2[NH:39][C:38]([CH3:44])=[N:37][C:36]=2[Cl:35])=[O:42])=[C:18]([F:34])[C:19]=1[O:24][C:25]1[CH:26]=[C:27]([C:28]#[N:29])[CH:30]=[C:31]([Cl:33])[CH:32]=1

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 671971663-{[3-(Aminomethyl)-6-bromo-2-fluorophenyl]oxy}-5-chlorobenzonitrileHCID 178432882HCID 178432882, Verbindung

Produkt 1

HCID 178432867HCID 178432867, VerbindungAusbeute 12,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

EDC (0.060 g, 0.311 mmol) and HOBT (0.042 g, 0.311 mmol) were added to a solution of 3-{[3-(aminomethyl)-6-bromo-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.111 g, 0.311 mmol) and 4-chloro-2-methyl-1H-imidazole-5-carboxylic acid (0.050 g, 0.311 mmol) in DMF (2 mL). The mixture was stirred at RT overnight. The reaction mixture was extracted with EtOAc and saturated sodium bicarbonate and the organic layer was dried over sodium sulfate and concentrated. Rerverse phase HPLC (acetonitrile:water with 0.1% formic acid) gave the title compound (0.019 g, 12%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.86 (br. s., 1H), 8.17 (br. s., 1H), 7.77-7.88 (m, 1H), 7.57-7.66 (m, 1H), 7.46-7.55 (m, 1H), 7.44 (br. s., 1H), 7.22-7.35 (m, 1H), 4.37-4.70 (m, 2H), 2.28 (s, 3H). LCMS: m/z 497, 499.

Aufarbeitung

  1. extractionThe reaction mixture was extracted with EtOAc and saturated sodium bicarbonate
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d611fc9608b34b1b99cab5caec5b2f16
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304419B2

Notizen zur Reaktion

Wird geladen…